The best family-friendly cottages on the Isle of Wight holiday cottages

The best family-friendly cottages on the Isle of Wight

With the next school holiday looming, it’s time to start planning your family getaway, and the Isle of Wight is a fantastic place for your half-term adventures. To save you from hours of searching for the perfect property, we’ve picked out a handful of our best options for those with young kids, teenagers and large families to make your life a little easier. What’s more, many of them are also dog-friendly, so you don’t need to leave any members of the team behind! Take a look at some of the best family-friendly cottages in the Isle of Wight:

The best cottages for young families

Worsley Cottage, sleeps 6, Isle of Wight

Worsley Cottage, sleeps 6

This stylish and well-equipped cottage is set in a peaceful hamlet, perfect for gentle walks through stunning countryside, playing in the garden or simply relaxing beside the open fire. When the sun is shining, you can make the most of the outdoor space, featuring a trampoline, slides and swings for the little ones, while the indoor play lounge is great for the when the weather isn’t quite so desirable.

Property highlights:

  • Wood burner
  • Sky TV
  • Front and rear gardens

Strawberry Cottage, Isle of Wight

Strawberry Cottage, sleeps 4 + 2 dogs

Only a stone’s throw from the beach, this cosy cottage is fantastic for young families at all times of year. With an enclosed garden, bright, spacious living area and plenty to explore along the coast, you’ll love being situated in a quiet village and heading out on seaside adventures.

Property highlights:

  • Bike/surfboard storage
  • Enclosed garden with wildflowers and perennials
  • Private drive for two cars

The best cottages for families with teenagers

Stanwell Barn Cottage, Isle of Wight

Stanwell Barn Cottage, sleeps 8 + 2 dogs

Set in an Area of Outstanding Natural Beauty, Stanwell Barn Cottage is a coastal escape that you’ll never forget. The barn conversion has been beautifully fashioned to create a modern living space, whilst retaining original features such as exposed beams and stone walls. The older children and adults will love the pool table and other activities in the games room - as well as the plethora of water sports - meaning you won’t be short on things to do on your stay!

Property highlights:

  • Wood burner
  • Games room
  • Enclosed garden with BBQ

The best cottages for large families

Little Orchard Cottage, Isle of Wight

Little Orchard Cottage, sleeps 9

Set just a 10-minute walk away from the sea, Little Orchard Cottage is a fantastic place to celebrate or get the wider family together. Explore the coast and countryside by foot or bicycle, visit the local towns and villages, and make the most of some of the best beaches on the Isle of Wight! With plenty of space both inside and out, there’s something to appeal to everyone on this getaway.

Property highlights:

  • Enclosed garden with BBQ and furniture
  • Downstairs bedroom/bathroom for accessibility
  • Half a mile away from the beach

Lucerne, Isle of Wight

Lucerne, sleeps 12 + 2 dogs

In the heart of Cowes lies the luxury escape of Lucerne, where lazy afternoons in the garden, strolls in the village and days out around the island are aplenty. There are lovely restaurants in the village for the days when you don’t fancy cooking up a feast, although we certainly recommend making the most of the well-equipped kitchen during your stay and the games room is sure to keep all ages entertained for hours.

Property highlights:

  • Games room
  • Wood burner
  • 4-star luxury

The best all rounders

Woodington Cottage, Isle of Wight

Woodington Cottage, sleeps 10 + 2 dogs

This Victorian-style villa, located within walking distance of the coast path, is a great place to get the family together for a celebration. The large garden is the perfect place to enjoy the mild climate, whilst inside, the living space boasts five spacious bedrooms, two bathrooms and a games room featuring table tennis, mini snooker and table-top hockey to unleash your competitive side.

Property highlights:

  • Hot tub available to hire
  • Games room
  • Large garden with furniture and BBQ

The Blacksmiths Shop, Isle of Wight

The Blacksmiths Shop, sleeps 4

This converted blacksmith shop is an ideal place from which to explore the attractions of the south coast of the island. The kids will love seeing the cows and sheep in the 400 acres of farmland, and visiting the seaside town of Ventnor, just a 5-minute drive away. Its cosy atmosphere will have you feeling at home in no time and you’ll want to bring the family back year after year.

Property highlights:

  • Set on a working farm
  • Private courtyard with furniture
  • Secure bike storage facilities

Still searching for the perfect family-friendly property this half term? Check out our full collection of cottages on the Isle of Wight, or head to our blog for inspiration of where to go and what to do!

Like it? Share it...

Read more like this

How well does the UK know its islands?

Ahoy brains of Britain! With our recent quiz we looked to find out how well the UK knows its islands – check out the results and see how you fare.

Days out on the Isle of Wight

From animal adventures to music festivals, theme parks to bike rides, we’ve put together a list of the top days out on the Isle of Wight to inspire your holiday.

The Isle of Wight's best cottages for Christmas

A holiday break at Christmas can be a real treat whether you spend it with close family or throw the invite wider family.
The Travel Chapter Limited, trading as | The Travel Chapter Limited is registered in England and Wales. | Registered office Travel Chapter House Gammaton Road Bideford EX39 4DF Company No. 02431506 | VAT reg: 143053210